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Information on EC 4.2.3.125 - alpha-muurolene synthase
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4.2.3.125 alpha-muurolene synthaseIUBMB Comments
The enzyme has been characterized from the fungus Coprinus cinereus. Also gives germacrene A and gamma-muurolene, see EC 4.2.3.23, germacrene-A synthase and EC 4.2.3.126, gamma-muurolene synthase.
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The enzyme appears in viruses and cellular organisms
Synonyms
Cop3, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Cop3
Cop3
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-
ambiguous
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = alpha-muurolene + diphosphate
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-
-
-
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate-diphosphate-lyase (cyclizing, alpha-muurolene-forming)
The enzyme has been characterized from the fungus Coprinus cinereus. Also gives germacrene A and gamma-muurolene, see EC 4.2.3.23, germacrene-A synthase and EC 4.2.3.126, gamma-muurolene synthase.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
-
recombinant Escherichia coli produces alpha-muurolene to 30% of total terpenoid compounds, but also other sesquiterpenes
-
?
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
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the major cyclization products of Cop3 and its loop mutants are derived from an E,E-germacradienyl cation formed after ionization and 1,10 cyclization of E,E-farnesyl diphosphate. alpha-Muurolene is 30% of the products formed from (2E,6E)-farnesyl diphosphate
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-
?
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
-
recombinant Escherichia coli produces alpha-muurolene to 30% of total terpenoid compounds, but also other sesquiterpenes
-
?
additional information
?
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product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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-
?
additional information
?
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product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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-
?
additional information
?
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-
seven different sesquiterpenes products, wild-type Cop3 also shows gamma-muurolene synthase activity, EC 4.2.3.126, and produces 12% gamma-muurolene and 35% gemacrene A, product of germacrene A synthase, EC 4.2.3.23, of total products from (2E,6E)-farnesyl diphosphate, product profiling by GC-MS analysis, overview
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-
?
additional information
?
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product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
-
the major cyclization products of Cop3 and its loop mutants are derived from an E,E-germacradienyl cation formed after ionization and 1,10 cyclization of E,E-farnesyl diphosphate. alpha-Muurolene is 30% of the products formed from (2E,6E)-farnesyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate
alpha-muurolene + diphosphate
-
-
-
?
additional information
?
-
product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
-
-
?
additional information
?
-
-
product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
-
-
?
additional information
?
-
-
seven different sesquiterpenes products, wild-type Cop3 also shows gamma-muurolene synthase activity, EC 4.2.3.126, and produces 12% gamma-muurolene and 35% gemacrene A, product of germacrene A synthase, EC 4.2.3.23, of total products from (2E,6E)-farnesyl diphosphate, product profiling by GC-MS analysis, overview
-
-
?
additional information
?
-
product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
the enzyme contains the metal-binding DDXXD motif
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
steady-state kinetics, overview
-
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
flesh and rind, expression analysis in several different genotypes, high level of alpha-muurolene formation in lines Eshkolit Ha'Amaqim and Arava, sesquiterpene compound profiles, detailed overview
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
role of the active site H-alpha1 loop in catalysis, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). AGR3_AGRAE
358
0
40819
Swiss-Prot
other Location (Reliability: 5)
TPS4_PHYPO
337
0
38751
Swiss-Prot
other Location (Reliability: 4)
CS_HELAN
555
0
64263
Swiss-Prot
other Location (Reliability: 4)
STS1_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38401
Swiss-Prot
other Location (Reliability: 3)
TPS1_PHYPO
334
0
38880
Swiss-Prot
other Location (Reliability: 3)
COP3_COPC7
Coprinopsis cinerea (strain Okayama-7 / 130 / ATCC MYA-4618 / FGSC 9003)
425
0
47766
Swiss-Prot
other Location (Reliability: 2)
AGR1_AGRAE
346
0
39574
Swiss-Prot
Mitochondrion (Reliability: 4)
STS10_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
336
0
38275
Swiss-Prot
other Location (Reliability: 4)
FARS_MAIZE
533
0
61534
Swiss-Prot
other Location (Reliability: 3)
STS2_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38419
Swiss-Prot
other Location (Reliability: 4)
A0A251T2E0_HELAN
555
0
64263
TrEMBL
other Location (Reliability: 4)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
structural homology modeling of Cop3 using the crystal structure of aristolochene synthase from Aspergillus terreus. Several polar side chains in the H-alpha1 loops of Cop4 and Cop3 move closer to side chains in the metal-binding DDXXD motif
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H255P
-
site-directed mutagenesis, modification of the H-alpha1 loop, the mutant shows highly altered product profile compared to the wild-type enzyme, it does no longer produce alpha-muurolene but large amounts of germacrene A (77%), overview
K251I
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site-directed mutagenesis, modification of the H-alpha1 loop, the mutant shows only slightly altered product profile compared to the wild-type enzyme, it produces also beta-copaene, cf. EC 4.2.3.127, overview
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of wild-type and mutant Cop3 in Escherichia coli strain JM109
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gene cop3, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli strain JM109 leading to production of alpha-muurolene
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Portnoy, V.; Benyamini, Y.; Bar, E.; Harel-Beja, R.; Gepstein, S.; Giovannoni, J.J.; Schaffer, A.A.; Burger, J.; Tadmor, Y.; Lewinsohn, E.; Katzir, N.
The molecular and biochemical basis for varietal variation in sesquiterpene content in melon (Cucumis melo L.) rinds
Plant Mol. Biol.
66
647-661
2008
Cucumis melo
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Agger, S.; Lopez-Gallego, F.; Schmidt-Dannert, C.
Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus
Mol. Microbiol.
72
1181-1195
2009
Coprinopsis cinerea (A8NE23), Coprinopsis cinerea, Coprinopsis cinerea ATCC MYA-4618 (A8NE23)
brenda
Lopez-Gallego, F.; Wawrzyn, G.; Schmidt-Dannert, C.
Selectivity of fungal sesquiterpene synthases: Role of the active sites H-1alpha loop in catalysis
Appl. Environ. Microbiol.
76
7723-7733
2010
Coprinopsis cinerea
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